The Politically Inspired Job Title Spreading Through Startups

In an article published this past summer, The Washington Post described a secretive members-only group on the West Coast meeting to discuss the latest updates and gossip in the tech industry. The article was referring to a very specific and self-selecting set of individuals : the chiefs of staff (CoS) of well-known startups. The Post’s account may be a bit dramatized ; I imagine a bunch of 20-something men and women clad in American Apparel t-shirts huddled in a dark lounge and keying into the latest industry activity while quietly judging who has real influence in their business.

What a CoS is varies widely between organizations. As if defining “business development” at a startup weren’t already difficult enough, the chief of staff has brought that challenge to a whole new level.

Chiefs of staff have existed in the political sector since the 1950s. The White House CoS, for example, is the highest ranking employee of the White House. Their role is to help the president manage communication channels, scheduling, advisory teams, and simple issues of access.

Chiefs of staff have gained momentum among tech companies large and small as the pace of growth quickens and efficiency and structure become necessities. So, what exactly is a CoS in the context of the tech world? What are their responsibilities? What should you look for when hiring a CoS? Is it a necessary function given the other, more specific problems and needs of startups?

As the chief of staff at Spring, I thought it would be helpful to answer these questions by offering a glimpse into my journey, my always-in-flux responsibilities at Spring, and my perspective on how the position is evolving.

A Brief History of Me

It’s easiest to describe my career as that of a generalist – or maybe a Renaissance man? I’ve worked with companies in capacities managing business development, sales, marketing, operations, recruiting, product, design, legal, fundraising, and more. Foursquare gave me the opportunity to witness firsthand how to create a well-oiled machine poised to solve problems and grow quickly. At Techstars, I worked cross-functionally with the class doing all of the above. Joining ChatID (now known as Welcom) as the first employee, I helped raise money from tier-one investors, build and launch our first product, pivot the business, sell to Fortune 500 brands, and grow the team. I joined Spring when the company had fewer than five employees to focus on building the supply side of our marketplace with the world’s top fashion brands while working cross-functionally with our marketing, product, and operation teams.

My transition to Spring’s chief of staff was a rather natural occurrence. I’d been providing coverage for gaps in the business and operations from very early in the company’s life. It’s the “do it all, do it fast” mindset that I believe is critical to a startup’s success. Startups, especially at the earliest stages, can do very well if they have an extra hand that is able to pick up the slack where no other full-time hire is focused.

The balancing act for a CoS in a quickly growing business is to fulfill the current needs of the CEO and company while keeping an eye toward building a team that can own and manage the focus area or project specifically over time.

Chief of Staff: A Critical Role

Here are a few reasons why the CoS is becoming a more recognized role among tech companies:

CoS provides an additional layer of structure without necessarily becoming the quintessential “gatekeeper.”

Startups need to move quickly . Time is the most critical asset. CoS handles areas of the company that have a direct impact on the business/product but do not always fit the core job descriptions of the rest of the team.

CEOs never have enough time to do it all themselves. The best CEOs, in my opinion, are leaders with whirlwinds of ideas who live in ceaseless deluges of creativity. CoS provides coverage for the CEO to run and explore new areas of opportunity without distracting or diverting resources from the rest of the company.

How the Functions Vary by Company

As much as the culture of a company matters in the creation of a CoS role, the CoS is more a byproduct of the company’s ever-changing needs. That is to say that while every high-growth startup has inherent differences in mission, product, team, culture, business, etc., they are all similar in the fact that the sheer pace of their growth justifies having someone who can maintain visibility of the CEO’s high-level vision while operating at the ground level.

The devil is in the details, and the CoS succeeds at facilitating the CEO’s vision (and tangential visions) while enabling other members of the leadership team to work together and get decisions made faster.

Having spoken to other CoSs, I know that the day-to-day responsibilities of the role can differ widely from one business to the next. One common theme is the CoS typically has wide access to sensitive data and key decision-makers across the organization. Here are a few examples of projects I work on:

The term “gatekeeper” has been used to describe the CoS, particularly in the world of politics. However, I would argue “facilitator” is a better description of how a CoS should actually perform their responsibilities. The foundation of this role for me is trust. Gaining the respect of an executive team and trust among colleagues doesn’t happen overnight. For this reason , the position can be difficult to hire for from the outside. Grooming a current employee is almost always a better option.

That being said, here are the traits that make a good CoS:

Trust

Multitasker

Entrepreneurial

Efficient with limited resources

Strong communicator

Confident in managing up

Ability to comfortably dive into most/any area of the business or product

Good sounding board for others in the company ; provides open, honest feedback

No ego ; helps employees understand how they can be useful instead of serving as a roadblock to the top

Getting Into the Role

I’ve seen these positions called many things with varying definitions internally and externally – e.g., “generalist”, “founder’s associate”, “chief administrative officer”, “chief of staff”, etc. Often, new startups typically know they need the extra support that comes from having a CoS, but the title seems too formal given the size of the company and the roles of the founding employees. Finding your way into a CoS position depends heavily on understanding the current needs and stage of the company.

Earlier-stage startups are prime for the “generalist” or “founder’s associate” role. This is not an executive assistant position as much as it is a facilitator of the CEO’s priorities. Working with a variety of teams requires a broad skill set and the flexibility to work intelligently on ad hoc projects. Speed is the greatest asset. I would also argue that a CoS could develop out of a variety of existing positions , like product, operations, business development, and marketing. A good CoS candidate will have deep exposure to certain aspects of the business but may need to prove their ability to work cross-functionally.

CoS Career Advancement

The CoS position can be a great grooming experience for an executive operational role in the business. Many CoSs go on to become vice presidents of operations, general managers, or something similar. Personally, I’m learning and gaining experience working alongside great founders and a fantastic team so that I can ultimately venture out to start my own company. Arming myself with the institutional knowledge that can only be gained by helping build a company from the ground up is critical to my future success as a founder and leader. In this regard, the role of CoS couldn’t be a better fit for aspiring entrepreneurs.

–

Are you a CoS in New York ? Reach out to me if you’d like to join a not-so-secretive group of chiefs of staff (scott@scottamenta.com). We’ll be meeting quarterly to discuss the ins and outs of our roles and learn from each other.

42Hire ("Don't Panic, Just Hire") is about how to simplify hiring. We share how businesses attract talent for their interests and how talented people take the next steps in their careers. This practitioner-first community has published 650+ writers. It was founded and is edited by David Smooke. 42Hire.com is part of the AMI publications blog network. Follow 42Hire on Twitter (@42Hire)